After he released his album with the Dancehall Doctors, he promised he would buy all the band members Harleys if the album sold a half-million copies. The album Tim McGraw and the Dancehall Doctors, sold 602,000 in its first week, and Tim bought three Harleys and a few vintage cars.

Tim fell in love with Faith while on the Spontaneous Combustion tour in 1995. He proposed to her in his trailer dressing room, and while he went out on stage, Faith wrote her answer, "Yes," on his mirror.

Tim and Kenny Chesney were once arrested after a concert in Orchard Park, NY. Chesney allegedly mounted a police horse, and Tim held back police officers in fear that Kenny would fall down. Tim was arrested on the suspicion of second degree assault, and menacing and resisting arrest. They were eventually cleared of all charges.